Molecular diversity of triphenylphosphine promoted reaction of electron-deficient alkynes and arylidene Meldrum acid(N,N’-dimethylbarbituric acid)  

作　　者：Ying Han Hui Zheng Yuan-Yuan Zhang Chao-Guo Yan 

机构地区：[1]College of Chemistry&Chemical Engineering,Yangzhou University,Yangzhou 225002,China

出　　处：《Chinese Chemical Letters》2020年第5期1337-1341,共5页中国化学快报（英文版）

基　　金：financially supported by the National Natural Science Foundation of China(No.21572196);the Priority Academic Program Development of Jiangsu Higher Education Institutions。

摘　　要：The three-component reaction of triphenylphosphine,dimethyl hex-2-en-4-ynedioate and arylidene N,N’-dimethylbarbituric acids in dry methylene dichloride at room temperature afforded trans-1,3-disubstituted 7,9-diazaspiro[4.5]dec-1-enes in good yields and with high diastereoselectivity.However,the similar three-component reaction with arylidene Meldrum acids resulted in a mixtures of cis/trans-1,2-disubstituted 7,9-dioxaspiro[4.5]dec-1-enes.Additionally,the three-component reaction of triphenylphosphine,dimethyl but-2-ynedioate and arylidene Meldrum acids gave polysubstituted 5-(triphe nyl-λ~5-phosphanylidene)cyclopenta-1,3-die nes.A plausible reaction mechanism was proposed for the formation of various products with different regioselectivity and diastereoselectivity.

关 键 词：PHOSPHINE Electron-deficient alkyne Meldrum acid Barbituric acid Spiro compound 

分 类 号：O627.51[理学—有机化学]